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Details

Stereochemistry UNKNOWN
Molecular Formula C17H23NO.ClH
Molecular Weight 293.832
Optical Activity ( + )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRANDAMINE HYDROCHLORIDE, (+)-

SMILES

Cl.CN(C)CCC1(C)OCCC2=C1CC3=C2C=CC=C3

InChI

InChIKey=OZWMTVPSSFWHIM-UHFFFAOYSA-N
InChI=1S/C17H23NO.ClH/c1-17(9-10-18(2)3)16-12-13-6-4-5-7-14(13)15(16)8-11-19-17;/h4-7H,8-12H2,1-3H3;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H23NO
Molecular Weight 257.3706
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Pirandamine is the potential antidepressant drug. It is a relatively selective inhibitor of the serotonin uptake mechanism and does not exhibit appreciable norepinephrine uptake blocking activity in contrast to the tricyclic antidepressant drugs imipramine and amitriptyline. Pirandamine is equivalent to amitriptyline and greater than imipramine in potency as a serotonin uptake blocker and a potentiator of central serotonin pharmacological actions, and in contrast, does not exhibit appreciable central anticholinergic effects. Pirandamine potentiated the behavioral effects of 5-hydroxytryptophan in mice. Pirandamine, in contrast to desimipramine and imipramine, did not prevent reserpine-induced hypothermia. The (-)-enantiomer of pirandamine retained the activity of the racemate; the (+I-enantiomer was much less effective.

Approval Year

PubMed

PubMed

TitleDatePubMed
Effects of tandamine and pirandamine, selective blockers of biogenic amine uptake mechanisms, on gastric acid secretion and ulcer formation in the rat.
1977-04-15
Pirandamine, a relatively selective 5-hydroxytryptamine uptake inhibitor.
1976-08
Effects of tandamine and pirandamine, new potential antidepressants, on the brain uptake of norepinephrine and 5-hydroxytryptamine and related activities.
1976-05-05
Patents

Patents

Substance Class Chemical
Created
by admin
on Tue Apr 01 16:43:20 GMT 2025
Edited
by admin
on Tue Apr 01 16:43:20 GMT 2025
Record UNII
XYN8PWH24Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDENO(2,1-C)PYRAN-1-ETHANAMINE, 1,3,4,9-TETRAHYDRO-N,N,1-TRIMETHYL-, HYDROCHLORIDE, (+)-
Preferred Name English
PIRANDAMINE HYDROCHLORIDE, (+)-
Common Name English
Code System Code Type Description
FDA UNII
XYN8PWH24Y
Created by admin on Tue Apr 01 16:43:20 GMT 2025 , Edited by admin on Tue Apr 01 16:43:20 GMT 2025
PRIMARY
CAS
60218-36-2
Created by admin on Tue Apr 01 16:43:20 GMT 2025 , Edited by admin on Tue Apr 01 16:43:20 GMT 2025
PRIMARY
Related Record Type Details
ENANTIOMER -> ENANTIOMER
RACEMATE -> ENANTIOMER